Sodium Hydroxide → HCID 58476269, compound

HRID 2045663Notes

Reaction equation

HRID 2045663 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14]C)=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:26])(=[O:25])[NH:23][CH3:24])[CH:17]=1.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1([CH3:27])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:26])(=[O:25])[NH:23][CH3:24])[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442598HCID 67442598, compound

Product 1

HCID 58476269HCID 58476269, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3,3-dimethyl-2-(3-(N-methylsulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (75 mg, 0.19 mmol) in tetrahydrofuran/methanol (2.5 mL/2.5 mL) was added 1M sodium hydroxide aqueous solution (2.89 mL, 2.89 mmol). The mixture was heated to reflux and stirred for 1.5 h. LC-MS indicated that 2005467-012-01 was consumed. The mixture was concentrated and the residue was dissolved in water. The aqueous layer was basified to pH=4 by 1M hydrochloric acid solution. The precipitated solid was filtered, and dried to give 56.7 mg of 3,3-dimethyl-2-(3-(N-methylsulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Yield: 78.5%. MS (ESI+APCI) M+1=375.2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customwas consumed
  4. concentrationThe mixture was concentrated
  5. dissolutionthe residue was dissolved in water
  6. filtrationThe precipitated solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-b26a450eb3094d23bd1ef93521d0d26f
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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